diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0ab17a67944..2a581edb9a3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -39,6 +39,7 @@ Docs: https://docs.openclaw.ai
 - Sandbox/Docker: apply custom bind mounts after workspace mounts and prioritize bind-source resolution on overlapping paths, so explicit workspace binds are no longer ignored. (#22669) Thanks @tasaankaeris.
 - Exec approvals/Forwarding: restore Discord text forwarding when component approvals are not configured, and carry request snapshots through resolve events so resolved notices still forward after cache misses/restarts. (#22988) Thanks @bubmiller.
 - Security/Elevated: match `tools.elevated.allowFrom` against sender identities only (not recipient `ctx.To`), closing a recipient-token bypass for `/elevated` authorization. (#11022) Thanks @coygeek.
+- Webchat/Sessions: preserve external session routing metadata when internal `chat.send` turns run under `webchat`, so explicit channel-keyed sessions (for example Telegram) no longer get rewritten to `webchat` and misroute follow-up delivery. (#23258) Thanks @binary64.
 - Config/Memory: allow `"mistral"` in `agents.defaults.memorySearch.provider` and `agents.defaults.memorySearch.fallback` schema validation. (#14934) Thanks @ThomsenDrake.
 - Security/Feishu: enforce ID-only allowlist matching for DM/group sender authorization, normalize Feishu ID prefixes during checks, and ignore mutable display names so display-name collisions cannot satisfy allowlist entries. This ships in the next npm release. Thanks @jiseoung for reporting.
 - Security/Group policy: harden `channels.*.groups.*.toolsBySender` matching by requiring explicit sender-key types (`id:`, `e164:`, `username:`, `name:`), preventing cross-identifier collisions across mutable/display-name fields while keeping legacy untyped keys on a deprecated ID-only path. This ships in the next npm release. Thanks @jiseoung for reporting.
diff --git a/src/auto-reply/reply/session.test.ts b/src/auto-reply/reply/session.test.ts
index aa442adb4eb..d73f2b1ad3a 100644
--- a/src/auto-reply/reply/session.test.ts
+++ b/src/auto-reply/reply/session.test.ts
@@ -1371,3 +1371,72 @@ describe("initSessionState stale threadId fallback", () => {
     expect(result.sessionEntry.lastThreadId).toBe(99);
   });
 });
+
+describe("initSessionState internal channel routing preservation", () => {
+  it("keeps persisted external lastChannel when OriginatingChannel is internal webchat", async () => {
+    const storePath = await createStorePath("preserve-external-channel-");
+    const sessionKey = "agent:main:telegram:group:12345";
+    await saveSessionStore(storePath, {
+      [sessionKey]: {
+        sessionId: "sess-1",
+        updatedAt: Date.now(),
+        lastChannel: "telegram",
+        lastTo: "group:12345",
+        deliveryContext: {
+          channel: "telegram",
+          to: "group:12345",
+        },
+      },
+    });
+    const cfg = { session: { store: storePath } } as OpenClawConfig;
+
+    const result = await initSessionState({
+      ctx: {
+        Body: "internal follow-up",
+        SessionKey: sessionKey,
+        OriginatingChannel: "webchat",
+      },
+      cfg,
+      commandAuthorized: true,
+    });
+
+    expect(result.sessionEntry.lastChannel).toBe("telegram");
+    expect(result.sessionEntry.deliveryContext?.channel).toBe("telegram");
+  });
+
+  it("uses session key channel hint when first turn is internal webchat", async () => {
+    const storePath = await createStorePath("session-key-channel-hint-");
+    const sessionKey = "agent:main:telegram:group:98765";
+    const cfg = { session: { store: storePath } } as OpenClawConfig;
+
+    const result = await initSessionState({
+      ctx: {
+        Body: "hello",
+        SessionKey: sessionKey,
+        OriginatingChannel: "webchat",
+      },
+      cfg,
+      commandAuthorized: true,
+    });
+
+    expect(result.sessionEntry.lastChannel).toBe("telegram");
+    expect(result.sessionEntry.deliveryContext?.channel).toBe("telegram");
+  });
+
+  it("keeps webchat channel for webchat/main sessions", async () => {
+    const storePath = await createStorePath("preserve-webchat-main-");
+    const cfg = { session: { store: storePath } } as OpenClawConfig;
+
+    const result = await initSessionState({
+      ctx: {
+        Body: "hello",
+        SessionKey: "agent:main:main",
+        OriginatingChannel: "webchat",
+      },
+      cfg,
+      commandAuthorized: true,
+    });
+
+    expect(result.sessionEntry.lastChannel).toBe("webchat");
+  });
+});
diff --git a/src/auto-reply/reply/session.ts b/src/auto-reply/reply/session.ts
index f644f47aa34..d95cfa825b7 100644
--- a/src/auto-reply/reply/session.ts
+++ b/src/auto-reply/reply/session.ts
@@ -31,7 +31,13 @@ import { deliverSessionMaintenanceWarning } from "../../infra/session-maintenanc
 import { createSubsystemLogger } from "../../logging/subsystem.js";
 import { getGlobalHookRunner } from "../../plugins/hook-runner-global.js";
 import { normalizeMainKey } from "../../routing/session-key.js";
+import { parseAgentSessionKey } from "../../sessions/session-key-utils.js";
 import { normalizeSessionDeliveryFields } from "../../utils/delivery-context.js";
+import {
+  INTERNAL_MESSAGE_CHANNEL,
+  isDeliverableMessageChannel,
+  normalizeMessageChannel,
+} from "../../utils/message-channel.js";
 import { resolveCommandAuthorization } from "../command-auth.js";
 import type { MsgContext, TemplateContext } from "../templating.js";
 import { normalizeInboundTextNewlines } from "./inbound-text.js";
@@ -39,6 +45,18 @@ import { stripMentions, stripStructuralPrefixes } from "./mentions.js";
 
 const log = createSubsystemLogger("session-init");
 
+function resolveSessionKeyChannelHint(sessionKey?: string): string | undefined {
+  const parsed = parseAgentSessionKey(sessionKey);
+  if (!parsed?.rest) {
+    return undefined;
+  }
+  const head = parsed.rest.split(":")[0]?.trim().toLowerCase();
+  if (!head || head === "main" || head === "cron" || head === "subagent" || head === "acp") {
+    return undefined;
+  }
+  return normalizeMessageChannel(head);
+}
+
 export type SessionInitResult = {
   sessionCtx: TemplateContext;
   sessionEntry: SessionEntry;
@@ -267,7 +285,28 @@ export async function initSessionState(params: {
 
   const baseEntry = !isNewSession && freshEntry ? entry : undefined;
   // Track the originating channel/to for announce routing (subagent announce-back).
-  const lastChannelRaw = (ctx.OriginatingChannel as string | undefined) || baseEntry?.lastChannel;
+  const originatingChannelRaw = ctx.OriginatingChannel as string | undefined;
+  const originatingChannel = normalizeMessageChannel(originatingChannelRaw);
+  const persistedChannel = normalizeMessageChannel(baseEntry?.lastChannel);
+  const sessionKeyChannelHint = resolveSessionKeyChannelHint(sessionKey);
+  let lastChannelRaw = originatingChannelRaw || baseEntry?.lastChannel;
+  // Internal webchat/system turns should not overwrite previously known external
+  // delivery routes (or explicit channel hints encoded in the session key).
+  if (originatingChannel === INTERNAL_MESSAGE_CHANNEL) {
+    if (
+      persistedChannel &&
+      persistedChannel !== INTERNAL_MESSAGE_CHANNEL &&
+      isDeliverableMessageChannel(persistedChannel)
+    ) {
+      lastChannelRaw = persistedChannel;
+    } else if (
+      sessionKeyChannelHint &&
+      sessionKeyChannelHint !== INTERNAL_MESSAGE_CHANNEL &&
+      isDeliverableMessageChannel(sessionKeyChannelHint)
+    ) {
+      lastChannelRaw = sessionKeyChannelHint;
+    }
+  }
   const lastToRaw = ctx.OriginatingTo || ctx.To || baseEntry?.lastTo;
   const lastAccountIdRaw = ctx.AccountId || baseEntry?.lastAccountId;
   // Only fall back to persisted threadId for thread sessions.  Non-thread